Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

• This invention concerns stable, solid antimicrobial compositions comprising 3-isothiazolones.
• EP-A-106,562 of April 25, 1984 shows similar solid formulations to Millar.
• EP-A-106,563 of April 25, 1984 shows stable, non-irritating, slow-release compositions containing 3-isothiazolones, an inert filler, and a high-melting solid, wax-like binder.
• a further object is to provide optionally salt-free, "stabilizer-free,” 3-isothiazolone microbicide compositions which are in solid form.
• the present invention provides in one aspect a composition
• a composition comprising a 3-isothiazolone compound and a carrier, which carrier is solid at room temperature and stabilizes said 3-isothiazolone against chemical decomposition.
• the 3-isothiazolones are of the formula wherein Y is a (C1-C18)alkyl or (C3-C12), preferably (C5-C8), cycloalkyl each optionally substituted with one or more of hydroxy, halo, cyano, alkylamino, dialkylamine, arylamino, carboxy, carbalkoxy, alkoxy, aryloxy, alkylthio, haloalkoxy, cycloalkylamino, carbamoxy, or isothiazolonyl; an unsubstituted or halo-substituted (C2-C8), preferably (C2-C4) alkenyl or alkynyl; a (C7-C10)aralky
• the invention provides a method of stabilizing a 3-isothiazolone against chemical decomposition comprising incorporating therewith a carrier as defined above, preferably at a ratio of isothiazolone to carrier of from 0.1:99.9 to 10:90.
• a method of preventing or inhibiting the growth of bacteria, fungi or algae in a locus susceptible or subject thereto comprising incorporating into or onto the locus, in an amount effective to adversely affect said growth, a composition as defined above.
• the invention also comprises in one other aspect the use of a carrier as defined above to stabilize a 3-isothiazolone against chemical decomposition.
• the carrier functions both as an agent to impart solidity and to impart stability. Many conventional carriers which would impart solidity do not also impart chemical stability, and those are not included in this invention. We have discovered a special class of carriers which have this dual function. We prefer those which are selected from the group consisting of polysaccharide polymers, cellulose polymers, derivatized cellulose polymers, polymers and copolymers of ethylene oxide and propylene oxide, polyurethane polymers having alternating hydrophobic and hydrophylic moieties, poly(maleic anhydride / methyl vinyl ether), polymethacrylic acid, and naphthalene formaldehyde condensates.
• the carriers are water soluble, and this is preferred.
• ratio of isothiazolone to carrier from about 0.1:99.9 to about 90:10 by weight, and more preferably from about 1.5:98.5 to about 25:75.
• compositions of the invention are the removal of the requirement for any salt stabilizer in some cases. This is surprising and unexpected because salts are generally used with most commercial 3-isothiazolones to stabilize them. Compositions free of the presence of salt or stabilizer (other than the carrier itself) are especially preferred.
• composition can also include one or more additives selected from the group consisting of deodorant, dye, sequestrant, fragrance, tableting aid, surfactant, additional stabilizer, additional antimicrobial compound, dispersant, antisettling agent, and excipient.
• additives selected from the group consisting of deodorant, dye, sequestrant, fragrance, tableting aid, surfactant, additional stabilizer, additional antimicrobial compound, dispersant, antisettling agent, and excipient.
• stable means that the compositions of the invention are stable for many months at room temperature, and for at least 3 days at 55°C as measured by retention of 3-isothiazolone compound.
• compositions of the invention can be in the form of a powder, bar, pellet, tablet, cast sheet or granules.
• compositions may be prepared by mixing a solution of the 3-isothiazolone in an organic solvent with the carrier and thereafter removing said solvent; mixing the isothiazolone and the carrier in the presence of water to form a slurry or a solution and thereafter removing the water by evaporation or spray drying.; melt blending the 3-isothiazolone and the carrier and thereafter molding or extruding said composition into a desired shape; or other suitable means.
• Example 2 In a manner similar to Example 1 18.2 g of the polyurethane and 0.22 g of oxyfluorfen were melted together on a steam bath. 1.62 g of molten isothiazolone was then blended in via hand stirring. Analysis of the product gave the following:
• Example 2 Following the procedure of Example 1 except using polyethyelene oxides of molecular weights ranging from 1450-20,000, (Carbowax, Union Carbide) in place of the polyurethane, the 2-n-octyl-3-isothiazolone was blended with the molten polyethylene oxides to yield solid formulations with AI between 9.5 and 12%.
• Methylene chloride was used to swell/dissolve the polyurethane (QR-735, Rohm and Haas) so that the blending could be done at a lower temperature, 35°C. On cooling to RT the material hardened and the residual solvent was removed by evaporation.
• Polyethylene oxide polymer (Polyox WSR 1105, Union Carbide), was suspended in an acetone solution of the 4:1 blend of 5-chloro-2-methyl-3-isothiazolone and 2-methyl-3-isothiazolone placed onto a Roto-Vap and the acetone stripped off. A product containing 4% AI was prepared. A sample was stored at 55°C for three days, which retained >75 % AI. A similar sample, prepared on sodium sulfate retained ⁇ 25 % AI under the same conditions.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Paints Or Removers (AREA)
• Plural Heterocyclic Compounds (AREA)
• Indole Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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Citations (4)

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• 1991
  • 1991-10-11 TW TW080108003A patent/TW212749B/zh active
  • 1991-10-30 US US07/784,852 patent/US5703105A/en not_active Expired - Lifetime
  • 1991-11-13 CA CA002055380A patent/CA2055380A1/en not_active Abandoned
  • 1991-11-26 BR BR919105131A patent/BR9105131A/pt not_active IP Right Cessation
  • 1991-12-04 DE DE69112193T patent/DE69112193T2/de not_active Expired - Lifetime
  • 1991-12-04 DK DK91311279.3T patent/DK0492843T3/da active
  • 1991-12-04 EP EP91311279A patent/EP0492843B1/de not_active Expired - Lifetime
  • 1991-12-04 NO NO914754A patent/NO179962C/no unknown
  • 1991-12-04 ES ES91311279T patent/ES2077185T3/es not_active Expired - Lifetime
  • 1991-12-04 AT AT91311279T patent/ATE126419T1/de not_active IP Right Cessation
  • 1991-12-06 NZ NZ240893A patent/NZ240893A/en unknown
  • 1991-12-06 AU AU88891/91A patent/AU656746B2/en not_active Ceased
  • 1991-12-09 FI FI915784A patent/FI97268C/fi not_active IP Right Cessation
  • 1991-12-09 IL IL10029191A patent/IL100291A/en not_active IP Right Cessation
  • 1991-12-09 IE IE427091A patent/IE68952B1/en not_active IP Right Cessation
  • 1991-12-09 PT PT99734A patent/PT99734B/pt not_active IP Right Cessation
  • 1991-12-10 JP JP35004391A patent/JP3248589B2/ja not_active Expired - Lifetime
  • 1991-12-10 MX MX9102485A patent/MX9102485A/es unknown
  • 1991-12-10 HU HU913879A patent/HU207786B/hu not_active IP Right Cessation
  • 1991-12-10 CN CN91111562A patent/CN1038979C/zh not_active Expired - Lifetime
  • 1991-12-10 KR KR1019910022537A patent/KR100225270B1/ko not_active IP Right Cessation
• 1995
  • 1995-06-06 US US08/471,888 patent/US5648086A/en not_active Expired - Lifetime
  • 1995-08-17 GR GR950402080T patent/GR3017149T3/el unknown

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